Procyanidin A2

• CAT Number: R005435
• CAS Number: 41743-41-3
• Molecular Formula: C30H24O12
• Molecular Weight: 576.51
• Purity: ≥95%
• IUPAC Name: (1R,5R,6R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
• InChI: InChI=1S/C30H24O12/c31-13-7-20(37)24-22(8-13)41-30(12-2-4-16(33)19(36)6-12)29(39)26(24)25-23(42-30)10-17(34)14-9-21(38)27(40-28(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,21,26-27,29,31-39H,9H2/t21-,26-,27-,29-,30+/m1/s1
• InChIKey: NSEWTSAADLNHNH-LSBOWGMISA-N
• SMILES: C1C(C(OC2=C3C4C(C(OC5=CC(=CC(=C45)O)O)(OC3=CC(=C21)O)C6=CC(=C(C=C6)O)O)O)C7=CC(=C(C=C7)O)O)O

Procyanidin A2 (CAS 41743-41-3)  is a natural flavanol dimer of (–)–epicatechin that is found in the horse chestnut, mountain cranberry, and other fruits with antioxidant, anti-inflammatory, antibacterial, antiproliferative, and antidiabetic properties. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals (IC50 = 5.08 μM) and inhibits STAT3 activation induced by platelet derived growth factor (PDGF) in primary rat vascular smooth muscle cells (VSMCs) when used at a concentration of 30 μg/ml.Procyanidin A2 inhibits growth of  S.aureus and E.coli (MICs = 62.5 and 62.5 μg/ml, respectively) and proliferation of human HepG2 liver hepatocellular carcinoma and HeLa cervical cancer cells (EC50s = 62.19 and 66.07 μg/ml, respectively). It also increases insulin secretion from primary mouse pancreatic islets when used at a concentration of 10 μM in vitro and inhibits bisphenol A-induced glucose increases in fasted mice when administered at a dose of 10 μmol/kg per day.

Reference

1.Jacques, David, et al. "Structure of the dimeric proanthocyanidin-A2 and its derivatives." Journal of the Chemical Society, Chemical Communications 15 (1973): 518-520.
2.Ibrahim, Sabrin RM, and Gamal A. Mohamed. "Litchi chinensis: medicinal uses, phytochemistry, and pharmacology." Journal of ethnopharmacology 174 (2015): 492-513.
3.Wen, Lingrong, et al. "Identification of flavonoids in litchi (Litchi chinensis Sonn.) leaf and evaluation of anticancer activities." Journal of functional foods 6 (2014): 555-563.
4.Zhang, Liudi, et al. "Inhibition of PDGF-BB-induced proliferation and migration in VSMCs by proanthocyanidin A2: Involvement of KDR and Jak-2/STAT-3/cPLA2 signaling pathways." Biomedicine & Pharmacotherapy 98 (2018): 847-855.
5.Ahangarpour, A., et al. "Preventive effects of procyanidin A2 on glucose homeostasis, pancreatic and duodenal homebox 1, and glucose transporter 2 gene expression disturbance induced by bisphenol A in male mice." J Physiol Pharmacol 67 (2016): 243-52.